


Luke, I Am Your Brother

by orphan_account



Category: Supernatural
Genre: Anal Sex, Bottom Dean Winchester, Cock Rings, Feminized Dean, Fluff and Smut, M/M, Oral Sex, Season 3, Sexual Roleplay, Strap-Ons, Supportive Dean, Top Sam Winchester, Trans Male Character, Trans Sam Winchester
Language: English
Status: Completed
Published: 2016-11-16
Updated: 2016-11-16
Packaged: 2018-08-31 08:15:43
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,640
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8571121
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: It's Dean's final year unless they can get out of his deal. And it's his birthday. So Dean asks for one special thing - roleplaying as Luke and Leia in the bedroom. But not how Sam assumes.





	

“Luke and Leia.”

 

Dean regretted the words as soon as they left his lips. No one else would have noticed, because no one else knew his baby brother like he did. 

 

But Dean saw. He saw as soon as the names of those famous siblings left his mouth. Sam kept smiling, but the corners of those rosy lips turned down, those big, wide kaleidoscope eyes drooping just a little. 

 

“Luke and Leia? That’s who you wanna be?” Sam asked in that voice Dean had learned to adore. 

 

“Sam, I-- I can pick someone else.”

 

“No, we made a deal and I don’t break my promises. It’s okay. Get the costumes and we’ll do it.” The smile was back now, full force, though Dean could see right through it. Even when Sam rose and pecked his cheek - he knew it wasn’t okay.

 

Sam wasn’t like other baby brothers. Of course, he was screaming his big brother’s name on a nightly basis as he came - but there was something far more unique about Sam Winchester. 

 

Maybe some DNA got twisted when Sam was cooking in their mother’s womb, or maybe it was something else, but either way, Sam came out missing a few key ingredients. He spent the next eighteen years getting called she, girl,  _ Samantha _ . 

 

Dean had known from an early age that Sam wasn’t like the girls in his school. Sam was special. She - at the time - roughhoused with the best of them, abhorred the dresses and bras their father awkwardly forced her into. Of course the time, and their general lack of education, made it so Dean didn’t have a word for what his sibling was feeling, and neither did Sam.

 

When he came to pick up his baby sister at college that fateful Halloween night, there was no hiding the shock. Sam looked  _ good _ .  Gone was the scrawny, awkward sibling in too-big jeans and a shirt that hid all of Sam’s curves. Pinned under Sam for just a second Dean saw - and felt - muscles that rippled, a hard chest that pounded with a strong, confident heart. 

 

The conversation was difficult for both parties in the car on the way to Jericho. It was in college that Sam found himself. He’d found like-minded people - people who put a name to the way he was feeling. He got into therapy, got on hormones, had his top surgery, and had been living happily as Samuel for years. 

 

Sam was scared, and Dean knew it. He didn’t need to say the words - he was scared Dean wouldn’t accept him, would call him a freak, would use his old name, his wrong pronouns… But Dean was proud. 

 

Sam cried when Dean gathered him in his arms in the car at that crappy rest stop in the middle of nowhere, kissed his cheek and called him little brother. 

 

The relationship came later. A drunken night of confessions and tequila kisses; Dean found himself truly head over heels for his not-so-little baby brother. They made it work, despite everything. It came as natural as breathing for Dean - just another way he could take care of his family, his Sammy.

 

Now here they were, two years later and right in the middle of what would be the final year of Dean’s life - provided they found no way out of the deal he made. Sam had asked Dean what he wanted for his birthday, and Dean - jokingly - said that he wanted to roleplay in the bedroom. 

 

When asked who he wanted to roleplay as, Dean popped off with a long time fantasy he’d had - Luke and Leia, his favorite film franchise and his dirty little kink. And now the reason he’d hurt Sam once more without intending to. 

 

Though Dean had repeated again and again that he was proud of Sam for his transition, he loved him no matter what, Sam still had his insecurities. It was to be expected; Dean had grown up with what he assumed was just a snot nosed sister, and an overnight reversal of that train of thought was trying on both of them at times. It had taken Sam six months of intimacy with Dean before he let his brother leave the light on during sex, and even longer to fully allow himself pleasure. 

 

And now, Dean screwed up months of working to equality with one fuck up - placing Sam in that box he’d fought so hard to escape from. There had to be a way to fix this. His final year; he wouldn’t let himself die with Sam hurting over a stupid sex fantasy.

 

A week passed without either brother bringing up the proposed birthday present. It was getting closer and closer to Dean’s birthday, the night they’d planned to play out whatever fantasy he wanted, and Dean was no closer to coming up with a solution.

 

Until it hit him. He was stretched out next to Sam in their shared bed in another no-name motel when the idea came to him. As quietly as he could, he rose from the bed and dug out Sam’s laptop, praying his new idea would work out.

 

**

 

_ “Can I come back to the hotel yet?” _ Sam whined.

 

“Give me one more hour, can you do that, Sammy?” Dean asked, slightly short of breath.

 

_ “It’s Sam… One hour and then I’m coming back whether you want me to or not. It’s your damn birthday, I don’t wanna spend it alone at a bar.”  _ Sam scolded.

 

Dean laughed a little. “I promise, it’ll be worth it. See you in an hour, Sam.” He hung up and tossed his phone on the side table, hurrying through his preparations once more.

 

**

 

One hour on the dot and Dean heard the door to the motel room unlock. He was hiding in the bathroom, listening intently for any sign of this going south. A low chuckle echoed through the room; Sam must have found the costume and note.

 

Dean gave him a few minutes to get into the costume before he opened up the bathroom door, stepping into the main room and leaning on the wall.

 

Sam looked up from fixing the belt that tied together the robes of the Luke Skywalker costume Dean had gotten for him. His jaw dropped and Dean felt a blush rise in his cheeks, self conscious for the first time that night.

 

He glanced down at himself, making sure nothing was sticking out. Of course the costume didn’t  _ quite _ fit - the bikini top of Leia’s slave outfit  _ was _ made for someone with actual breasts and Dean had opted out of a wig to lengthen his hair. Instead he’d just put in a few delicate gold strands and applied makeup as well as he could, hoping Sam would still make the connection. 

 

Unable to resist, he’d made one minor adjustment: the chain that hung down from the thick gold collar around his neck was tucked into the bottom of the bikini. He’d attached it to a cock ring he’d put on, all hidden within the folds of purple fabric pooling between his legs and around his bare feet.

 

“De-- you look--”

 

“Please, Luke,” Dean said suddenly, cutting Sam off mid sentence. He stumbled forward and fell into Sam’s arms, looking up at him with big eyes. “Have you come to save me, brother?”

 

A slow smile curved Sam’s mouth upward, his eyes glinting playfully. “Maybe… For a price.”

 

Dean gasped, sliding down the length of Sam’s body until his knees hit the carpet. “And what price is that, Luke?”

 

Sam ran his fingers through Dean’s hair, fisting it and tugging back, baring Dean’s neck. “If I save you from your captor, you must agree to be  _ my _ slave, sister.” 

 

Dean shivered, his eyes fluttering shut. “Yes, sir,” He whispered. 

 

Sam grabbed the chain and tugged to get Dean back on his feet. 

 

Dean rose quickly, hissing in surprise. He flushed red and grabbed the fabric over his groin, moving it aside so Sam could see the ring nestled at the base of his already aching cock. 

 

“Well then, someone’s a good girl,” Sam growled, reaching out and giving Dean’s cock a firm stroke. 

 

Dean’s eyes rolled back and he slumped forward onto Sam, a shiver running through him. “Please,” He whispered.

 

“Please what?”

 

“Fuck me.” 

 

The silence stretched on so long that Dean was worried he’d overstepped. He looked up at Sam, searching his face for any sign of reluctance or discomfort, but Sam was - for once - unreadable.

 

“Are you sure?” He finally whispered, and Dean smiled softly.

 

They’d played with toys before; Dean wasn’t ashamed to admit he loved being filled with anything they could get their hands on - but Sam had always balked at the idea of using a strap on, though that had been one of the first sexual instruments that they had purchased. Sam had always said a packer was one thing - it was functional, but they didn’t  _ need _ to use a strap on, Dean had a perfectly fine cock between his legs that Sam was more than happy to ride during sex. 

 

Dean hung his head, stepping close to Sam. He splayed his hands on Sam’s chest and slid them down slowly, curling one hand around the bulge in the loose cotton of Sam’s pants and giving a gently squeeze. “Of course I’m sure. And I’m all ready for you too.”

 

“Is that so?” Sam breathed, pulling Dean tight to his body. He slid his hands over Dean’s bare back, finding the flowing fabric and slipping under it. He spread Dean’s cheeks, his thumb brushing over the plug nestled between them. 

 

“You really thought this out,” Sam whispered, a barely noticeable quiver in his voice.

 

“Well, it is my birthday present, I figured I should be ready, in case you said yes.”

 

Sam’s mouth covered Dean’s before another word could be spoken. The kiss was rough, lips bitten, teeth clashing. All delicacy was gone from Sam then, he gripped Dean’s hips and shoved him onto the bed, following quickly so their mouths were only separated for a second. 

 

Calloused fingers stroked over Dean’s bare inner thighs, up, pressing against his perineum before finding the plug’s base and pushing it deeper.

 

Dean gave a guttural moan, his hips bucking upwards, needing more stimulation than the toy offered. 

 

“Please, Luke -” He panted through bite reddened lips, fingers clawing at the fabric that kept Sam’s skin hidden from his touch.

 

“Patience, my sweet,” Sam breathed with a calmness that made Dean want to scream. Sam pressed his hips down with wide hands, holding him still as his mouth roamed over Dean’s neck, lapping at the sweat already streaking its way across the freckled skin. 

 

“Damnit --” Dean hissed, digging his fingers into Sam’s shoulders.

 

Sam pulled back, cocking his head a little. “Tsk, tsk. It’s unbecoming of a lady to use such language. Maybe we should put that mouth to a better use.”

 

Dean’s throat closed, a soft whimper rasping its way out. He nodded, sliding his hands down to grip Sam’s ass once more. “I think you should.”

 

Sam stood fast enough that Dean cried out in surprise, reaching for him. He stilled though, lifting himself onto his elbows to watch Sam. He spread his thighs a little further and reached down, rubbing at his cock through the fake silk, the feel of it delightful as it dragged over his cock head.

 

Sam wandered over to their duffel bag and dug in it for a moment, giving Dean a clear view of his ass. He turned back and climbed back onto the bed, slipping the strap on under the spare pillow and fumbling with the buckle on the pants.

 

Dean reached up, helping him undo the pants and push those and his boxers down around his knees. Without waiting for the command, Dean leaned forward, running his tongue along Sam’s already damp slit. He gripped Sam’s hips, biting gently and sucking as he moved up, his nose brushing Sam’s swollen dick before taking it into his mouth. 

 

The whimper that erupted from Sam’s throat was well worth it. Fingers dug into Dean’s short hair, tugging, nails scraping his scalp as Sam’s hips bucked forward, his thighs shaking with the stimulation.

  
Always the shy one, it’d taken months for Sam to let Dean give him oral. Even now it was a rare treat, and Dean was always grateful. He shifted, freeing the swollen tip from his mouth before pushing Sam flat onto his back. 

  
A breathy laugh escaped. “Pushy for a slave girl, aren’t you?” Sam gasped. 

 

“Shut up,” Was all Dean managed before his mouth was busy again, teeth lightly scraping as he slipped his tongue into Sam’s sweet center. 

 

“Fuck-- You’re killing me,” Sam grumbled, his hips bucking upwards as another gush of fluid dribbled down Dean’s chin. 

  
Dean laughed, driving his tongue deeper before sliding up, capturing Sam’s dick once more and giving a hearty suck.

 

The bed creaked as Sam writhed on it, one hand gripping Dean’s head, the other white knuckling the edge of the mattress. Sam’s hips bucked sporadically, his breath coming in short punches as his tears formed at the corner of his eyes. Oversensitive on a good day, oral always had him falling apart in the best of ways. 

 

Sam’s throat clicked, his short nails biting a little harder into Dean’s scalp. “Gonna come,” He croaked. 

 

Dean grunted an affirmative, sucking and licking with more fervor than ever. Another hot gush of fluid to add to the growing wet spot on the bed and Sam was falling over the edge, groaning and panting, his entire body jerking as the waves of pleasure washed over him. 

 

It wasn’t until Sam sobbed weakly, pushing at Dean’s ribs with his knees, that Dean freed his throbbing dick. He moved up, catching Sam’s mouth in a messy kiss, lips and chin wet with Sam’s release.

 

Sam slid his hands down, under the fabric, and squeezed Dean’s ass as hard as he could manage, short nails biting into that freckled flesh he’d smacked more times than he could count. Dean groaned into his mouth, a needy sound that had Sam’s stomach tying itself in knots. 

 

Not to be controlled easily, Dean put up a bit of a struggle when Sam tried to flip them over. Short nails scratching skin, teeth biting possessive bruises into necks and shoulders, Sam couldn’t help the smirk that crossed his face when Dean was finally pinned under his body.

 

He squared his hips and sat down over Dean’s groin, grinding downward as Dean’s hips jerked up.

 

“You ready?” Sam asked, hesitation crossing his face for the first time since they started. 

 

Dean nodded, sliding his hands upward to Sam’s shoulders. “You know I am. Come on, brother… You know you wanna fuck me senseless.”

 

Sam shuddered, moving off Dean. He snagged the strap on from where he’d hidden it and turned so his back was to Dean as he put it on. 

 

Dean smiled a little, reaching down and stroking himself under the fabric as he watched. 

 

“You know you’re hot as hell when you’re being shy, Sammy.” Dean teased a little, earning a half hearted bitchface thrown over his shoulder.

 

Dean could see Sam worrying his bottom lip between his teeth when he turned around, his eyes downcast. It was a sure sign of either self-consciousness or thoughtfulness, and Dean assumed the latter. He smiled wider, letting his eyes rake up and down Sam’s body. 

 

Still clad in the Skywalker costume, Sam had fixed the pants with one exception, his cock stood proud out the front, a flesh tone one that they’d picked together. Dean knew, hidden behind the base of it was a second piece extending into Sam, a perfect way to get pleasure as much as giving it. 

 

Dean reached out, grabbing Sam’s hips and tugging until Sam’s knees hit the mattress. He leaned down, wrapping his lips around the cock and bobbing his head, using enough force to move the extension inside Sam.

 

Their eyes met for a moment and Sam smiled, a small gasp escaping as it moved once more. He gave a nod and Dean moved back, flipping onto his stomach and raising his hips up. The fabric slipped to the side of his hip, exposing his bare ass to the cool air of the motel room. 

 

Sam’s big hands warmed him quickly though, kneading and spreading his cheeks as Sam settled behind him. He tugged the plug out slowly, running his thumb over Dean’s fluttering entrance. He huffed a laugh, leaning down to press a kiss to Dean’s exposed back. 

 

“What’s so funny?” Dean whispered, his voice muffled by the pillow he was nuzzling.

 

“I feel like I should make some sort of lightsaber joke here,” Sam admitted, applying a little extra lube to Dean’s hole and the strap on.

 

Dean laughed, turning his head enough to look at Sam. “Thank you, by the way… For this. I know roleplaying isn’t your thing.”

 

Sam smiled a little. “You’re the one wearing the bikini.” He raised himself up on his knees and pressed the blunt head of the strap on against Dean’s rim, watching it flex like it was trying to take him in. He gasped when it hit him.

“Aha! I don’t need to make a lightsaber joke.”

 

Dean groaned, turning to look at Sam again with a half murderous smile. “Would you just fuck me? You’re killing me here.”

 

“May the Force be with you.”

 

Dean’s smile wavered. “Actually, Luke never said that. And definitely not to Leia. You know, most people misattribute the quote, or who said it. Most people think it was Obi-Wan, but in reality it was General Dodonna in A New Hope. I mean, Han said it to Luke later on in the same movie, but it’s not something that Luke ever said. You know, another thing that they screw up with that quote a lot is --”

 

“Dean, shut up,” Sam said, cutting him off mid sentence. Before Dean could argue or - god forbid - continue ranting on his error, Sam pushed in, cutting off any other chance for ranting from Dean.

 

He picked up a steady pace, hands gripping Dean’s hips. Dean glanced back and laughed breathily. “Don’t look so happy, Sammy,” He teased.

 

Sam glared at him again. “You know this is harder than it looks. So, shut up,” He mumbled, his cheeks burning with embarrassment. 

 

Dean smiled a little. He reached back, placing a hand on Sam’s thigh. “Pull out.”

 

When Sam did, he turned around and pulled Sam into a kiss before guiding him into a lying position on the bed. “Easier this way,” He explained.   
  


Without further discussion Dean straddled Sam’s hips, sinking down until the strap on was nestled completely inside him. He leaned over, pressing another kiss to Sam’s mouth. 

 

“Plus, this way I get to watch you while we fuck, you know I think you look so good when you come,” He mumbled against Sam’s mouth.

 

“How do you know this’ll make me come?” Sam wondered, setting his hands lightly on Dean’s thighs.

 

Dean lifted up and sank back onto the cock with a groan, smirking when Sam’s hips jerked upward. “Because I know your body, little brother. I know what makes you feel good, and I can do it no matter what we’re using.” 

 

He grabbed the headboard and began to ride Sam then, his other hand splayed on Sam’s heaving chest. 

 

Sam pumped his hips upward, holding tight to Dean’s thighs, nails biting into the pale skin as his feet slipped on the cotton sheets of the bed, struggling for leverage.

 

The headboard banged against the wall, mattress squeaking in the tell-tale rhythm of their intimacy. Sam’s chest was heaving, his hips jerking upward to meet Dean’s downward thrusts. Dean’s body was soaked with sweat - he couldn’t imagine how hot Sam was in that costume, but if the dampness of his shaggy hair was any sign --

 

The orgasm took both of them by surprise. Dean thrust down hard, forcing the entirety of the cock into him. He fought with the ring around his aching cock, fucking himself down onto Sam’s lap as fast as he could manage. Sam sat up, reaching down and unhooking the ring with a surprising ease. 

 

His large hand wrapped around Dean’s cock and began to stroke him, hard and fast. Their lips met, chests heaving together as Dean came hard, screaming into Sam’s open mouth. Sam groaned in response, snapping his hips upward hard and fast to fuck Dean through the orgasm, and bring his own on.

 

Dean was just coming down from his when Sam’s body went rigid. The hand on Dean’s back tightened, digging scratches across his shoulder blade as Sam’s orgasm hit. He curled his arms around Sam, holding him tightly and riding the cock despite his oversensitivity, helping Sam through his climax.

 

Dean pulled off the strap on with a groan and yanked off the costume. Sam did the same, albeit with a little more trouble, so Dean helped. When they were both nude, Sam tugged Dean close, kissing his mouth.

 

“Thank you,” He whispered.

 

“For what?” Dean’s reply was sleepy, spoken against Sam’s shoulder. 

 

“Doing what you did today - letting me be Luke.”

 

“No - I was glad to. It was a nice way to roleplay. Thanks for the good birthday, Sammy.”

 

“Happy birthday, Dean,” Sam murmured, wiggling down to kiss Dean’s mouth.

 

They were silent, each nearing his own sleep, when Dean spoke.

 

“But you really thought Luke said ‘May the Force be with you?’ Sam, I had to have taught you better. We should marathon the movies if you can’t remember, I--”

  
Sam groaned, grabbing a pillow from the side of the bed and slapping it over Dean’s face to shut him up.


End file.
